Thenyl ureas



United States THENYL UREAS David J. Beaver, Richmond Heights, and Paul J. Stoiiel, St. Louis, Mo., assignorsto Monsanto Uiemicai Comparry, St. Louis, Mo., a corporation of Delaware No Drawing. Application July 23, 1956 Serial No. 599,335

Claims. (Cl. 260-3323) This invention relates to new and useful thenyl ureas and to processes for making same.

In accordance with this invention it has been found that thenyl ureas of the structure wherein a, b, and c are halogen or hydrogen, wherein X is sulfur or oxygen, and wherein at least two of said a, b and 0 substituents are halogen, are highly useful These thenyl ureas are prepared by reacting a-thenyl amine with a compound of the structure temperature of the system.

As illustrative of the new compounds and the preparation thereof is the following:

Example I The product on drying is -(3,4-dichlorophenyl) N'-(otthenyl) urea (white granules, M. P. 1698-1705 C., yield=99%).

Example 11 Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate Example IV Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a chemically equiva- 2,865,929 Patented Dec. 23, 1958 lent amount of 3,S-dichlorophenylisocyanate, there is obtained N-(3,5-dichlorophenyl) N ta-thenyl) urea.

Example V Employing .the procedure of Example I but replacing fatty acid content analyzes Oleic and linoleic acid w about 46% Stearic acid about 14% Palmitic acidu about 30% Lower fatty acids (myristic, lauric, etc.) about 10%] in a weight ratio of one part to 50 parts soap. Aliquots Compound/Concentration, p. p. m 10 1 N-(3,4-dichlorophenyl) N-(a-theny1) urea none none.

The same control of Micrococcus pyogenes var. aureus is obtained by replacing N-(3,4-dichlorophenyl) N'-(otthenyl) urea with an equal weight of N-(3,5-dichlorophenyl) N'-(a-thenyl) urea and N-(3,4,5-trichlorophenyl) N'-(a-thenyl) urea. Good control of Micrococcus pyogenes var. aureus is obtained by replacing N-(3,4- dichlorophenyl) N'-(a-thenyl) urea with an equal weight of N-(3,4-dibromophenyl) N'-(a-thenyl) urea and N- (3,4-dichlorophenyl) N'-(a-thenyl) thiourea.

Replacing the foregoing Ivory brand soap with an equal weight of a Lux brand solid neutral white toilet soap (a mixture of alkali metal salts of fatty acids whose fatty acid content analyzes about 45% oleic and linoleic acid, about 30% palmitic acid, about 10% stearic acid, and about 15% lower fatty acids), the same results are obtained. The same results are also obtained using instead of a solid soap a liquid soap, such as that having a 40% alkali metal fatty acid soap content prepared from an alkali metal compound and a mixture of fatty acids obtained from a mixture of olive oil. Other alkali metal fatty acid soaps may also be used, e.

detergent soap composition have been found to yield eifective antiseptic detergent soap compositions. Amounts as low as 0.5 to 1% by weight based on the weight of the detergent soap have proved satisfactory. However, it is preferred to employ these urea derivatives in amounts in the order of 1 to 5% by weight based on the detergent soap. While larger amounts, as for example up to 10% by weight, may be employed the upper limit will be determined by practical considerations. Various colors, antioxidants, perfumes, water softeners, emollients, and the like, may be included where desirable in 1. Thenyl ureas of the structure wherein X is selected from the group consisting of sulfur and oxygen, wherein a, b and 0, respectively, are selected from the group consisting of hydrogen and halogen, and wherein the substituents'a, b and 0 total at least two halogen atoms, the said halogen atom being selected from the group consisting of chlorine and bromine.

2. N-(3,4-dichlorophenyl) N-(a-thenyl) urea.

3. N-(3,4-dichlorophenyl) N'-(a-thenyl) thiourea.

4. N-(3,4,5-trichlorophenyl) N'-(a-thenyl) urea.

detergent, soap as used herein is ern 5. The process of making the compound of claim 1, which comprises reacting urth nyl amine, with a com: pound of the structure a- --NO X wherein X is selected from the group consisting of oxygen and sulfur, wherein a, b and c are selected from the group consisting of hydrogen and halogen, and wherein the substituents a, b and c total at least two halogen atoms, in the presence of an inert organic solvent at a temperature in the range of room temperature to the refluxing temperature of the system, the said halogen atom being selected from the group consisting of chlorine and bromine.

References Cited-in the file of this patent UNITED STATES PATENTS Hartough Dec. 12, 1950 Searle Mar. 15, 1955 Swakon June 14, 1955 OTHER REFERENCES McKay: Can. J. Chem., 302227 (1952). 

1. THENYL UREAS OF THE STRUCTURE 